As the Inside-Out Prison Exchange Program continues to expand across correctional and educational institutions worldwide, instructors face the challenge of assessing the impact of these classes. Scholarship consistently describes the Inside-Out program as life-changing and transformative but often fails to provide measures that document this impact and how it manifests in the course. This study provides a nuanced understanding of the experiences of students enrolled in an Inside-Out Prison Exchange Program over a 3-year period (n = 87). Pre-and posttest surveys as well as 6-month follow-up interviews allow assessment of the program on student outcomes. Results demonstrate that initial criminal stigma perceptions held by Outside students of their Inside peers were quickly replaced by bonds that broke and interrupted deeply held beliefs of the criminal justice system and those caught in it. The relationships formed during the semester-long course also demonstrate an outcome that is not often accounted for in other prison-based programs. Furthermore, insights from students illuminated the importance of breaking down criminal stigma to inform and change the way we approach punishment and policy today.